My danger zone is the corners of my mouth, so leave a neutral facial expression and make a pass straight over. If I make an expression that pulls the skin tight, I'll be in trouble. I've always found simple alum to be the thing that helps - it dries the area out and makes the skin taut so the hairs that are now kinda under the skin can at least have a chance of making it through over the coming hours.
I also get hot and bothered skin from fencing where my mask meets my jawline. Occasional ingrowers as a result and found a spot treatment stick from L'Oreal - a metal roller ball and some sorta liquid, which was probably salicylic acid amongst other things.
... or, use Pashana Aftershave and once dried a couple more dabs of the stuff on the affected area. Healing aftershave!
Sometimes you've just gotta accept a single pass north/south shave and be done with "good enough". The fun there is to find a razor/blade combo and hone technique so that the one single pass is as good as a two pass. I used to have that proper nailed down with a 1912 but rarely find that same pleasure with a double-edged razor, even with the "Gillette slide".
Heal up, buddy! Tools for the job - if 3x with glasses works, carry on. Of course, if the company you keep all have aging eyesight ... well, a close shave matters somewhat less!